


If Only I'd Asked...

by pherryt



Category: Supernatural
Genre: Ash - Freeform, Bobby SInger - Freeform, Changing POV's, Charlie Bradbury - Freeform, Chef Benny, Chistmas Fluff, Denny - Freeform, Ellen Harvelle - Freeform, F/M, First Kiss, Garth fitzerald IV, Jo Harvelle - Freeform, M/M, Mechanic Dean, Misunderstandings, Mutual Pining, Other minor characters - Freeform, Pining, Pretend Boyfriends, Sam helps, Sick Sam, Sorento, castiel - Freeform, eileen and andrea plot, everyone ships it
Language: English
Status: Completed
Published: 2016-11-26
Updated: 2016-11-26
Packaged: 2018-09-02 10:26:58
Rating: General Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 7,119
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/8664184
Author URL: https://archiveofourown.org/users/pherryt/pseuds/pherryt
Summary: Sam convinces Dean to try a new place for lunch which quickly becomes their new favorite. Part of that's the good food, and some of it's the cook he keeps catching a glimpse of...but the mans already taken, apparently, so now Dean's pining and his friends can't take it anymore. Especially since they can tell the cook is pining right on back. So what's holding them back?





	

**Author's Note:**

  * For [AutumnSwitch](https://archiveofourown.org/users/AutumnSwitch/gifts).



> This is the winning fic prompt for the contest/giveway I ran: 
> 
> Do you feel comfortable writing a Dean/Benny pretend boyfriends, mutual pining thing? #Christmas fluff (but heavy on the mutual pining?) LOL 
> 
> It was supposed to be between 2500 and 5k but it uh, kinda got away from me. I hope you all like it :D

When all was said and done, if somebody wanted to point fingers, they could blame it all on Sam. Not that anyone _was_ blaming. There might have been pointing, but it was usually accompanied with the words, “Thanks, man,” from one brother, followed by, “You’re welcome,” from the other.

“You have to try this place, Dean, I swear to god, it’s fantastic!” Sam’s enthusiasm was catching, but Dean didn’t want to let on.

“Yeah right, Sammy, it’s probably just rabbit food.”

“Nope, I promise. Just, try it this once, okay?” Dean grunted and acquiesced and the two of them made their way to the Impala, Sam giving directions to the Cajun place only a few minutes’ drive away. They pulled into the lot and parked, Dean staring out the windshield at the simple looking restaurant before him.

“You better be right about this, Sam.”

“Course I’m right. When am I ever wrong?”

“We-ell,” Dean started with a grin, letting it drop after Sam sent him one of his patented bitch faces.  And that was the first time he’d stepped into Benny’s. It was just as good as Sam had promised, being a mixture of some good, old fashioned cooking and various Cajun dishes. Sam just laughed the first time Dean bit into something a little spicier than he had anticipated.

It wasn’t long before going to Benny’s was a daily tradition, with Sam and Dean meeting up for lunch. Eventually, knowledge of the place spread out through their circle of friends and they found themselves all going there for meals rather than one of their usual restaurants’ more often than not.

Occasionally, Dean caught glimpses of the burly cook who made the food the place was famous for. Those were the days the place was shorthanded, and he would bring out their meals himself. Dean may, or may not have been a bit smitten with the man.

Maybe. Not that he was going to admit that to anyone. Least of all Sam, who would crow about it somehow, Dean was sure. ‘sides, he didn’t even know anything about the guy, not even his name. Somehow, in their brief talks, it just never came up.

But he couldn’t seem to stop himself from craning his neck every time those double doors swung open. Sometimes he came out himself and then Dean would get a nice little eyeful, while other times, Dean had to be content with catching what glimpses he could. The man moved with such assurance and grace in the kitchen, and had such kind, but often sad looking eyes, that Dean was often struck dumb just from the sight of him.

Of course, being a peeping tom kind of backfired on him, the day he saw the cook and the waitress being overly familiar with each other. Any thoughts he had of trying to chat the guy up, see if they had anything in common had been nipped in the proverbial bud.

Didn’t stop him from looking though, a fact that his brother too much joy in pointing out more than once.

Fuck, he was screwed, wasn’t he?

* * *

Benny paused in the kitchen as Andrea sidled up to him. He flicked a glance at her and then back to the stove. He didn’t say anything and his ex-wife snickered. He knew what she was going to say and he resigned himself to it, his stomach twisting in knots.

“He’s back, you know.”

“Don’t know what yer talkin’ about, cher.” He deflected. She snorted, somehow making the sound delicate, and swatted him on the ass with a towel.

“You know damn well who I’m talkin’ about, Benny Lafitte, so don’t go playin’ innocent with me.” She grabbed him by the shoulders and shoved him towards the swing doors leading out of the kitchen. She took his chin and guided his gaze right on out the little round window, to where their newest regulars were sitting at their usual table. Benny’s breath caught at the sight of the green-eyed man throwing himself back into an unabashed, full body laugh.

“His name is Dean.” She whispered into his ear. Benny grunted, staring through the portal, the effort to pull his gaze away from the sight of the freckled man was immense, but he managed it. He turned back to the stove and got back to work. Andrea sighed and rolled her eyes, pushing out the door to take their orders.

Benny did pause then, watching the door swing back and forth, catching broken glimpses of the green-eyed man in the company of the taller one. Always, they came together, sat together, ate together. The man was not unattached, so he didn’t see why Andrea kept insisting in bringing him up.

The door slowed to a stop and he turned his attention back to his job, grateful that what he was currently working on wouldn’t have suffered for a few minutes of inattention and resolved to put the green-eyed man – Dean – out of his mind.

As he finished and plated the meal, slapping at the bell to call Andrea back for the delivery, Benny came to the sinking realization that he hadn’t really been all that successful in his attempts to forget about Dean. It didn’t make any sense. After all, he knew nothing about the man other than that he liked the food here – which, honestly, made Benny damn proud - he already had someone, had a wonderful smile, and beautiful eyes and a boisterous laugh, his name was Dean and oh, right, he already had someone. So, it wasn’t worth pining over, right?

Oh god, he was royally fucked, wasn’t he?

* * *

And that should have been that. That should have been the state of affairs for who knew how long. Probably forever, considering the two stubborn parties involved. The two men who were so quick to jump to conclusions – mistaken conclusions of course.

But neither Andrea nor Sam were oblivious to the mutual pining going on. And as Dean’s friends continued to patronize the place, neither were they. Hence the plan was born. Little by little, with their efforts, Dean and Benny grew to know each other. Snippets of conversation here and there, each helping to paint a picture of the other one word and glance at a time.

Dean finally learned Benny’s name, which then came with the realization that Benny was more than just the cook, while Benny learned that Dean was not only a mechanic – he’d found his eyes caught on a grease smudge on Deans cheek or his fingers more than once – but actually owned his own garage.

Frustratingly – for _everyone_ involved - it never went further than that except to make the mutual pining worse. It had been months now – months for God’s sake! – with summer making way for fall, then winter. It was December and they were no closer to a resolution on the matter than when they’d stepped in back in July. Sam let his head drop on the counter as Eileen carded fingers through his hair. “I can’t take it anymore. Dean won’t _listen_ to me. He actually thinks Benny isn’t interested in him, when a _blind_ man could tell that he was!”

“Sam, honey, I can’t read your lips when your hair covers your face.” Sam groaned and she felt the vibration of it through her fingertips. She decided to just let him vent. It would do him good. And if he could get it out of his system, then it would also do _her_ some good. In the meantime, without having to hear Sam’s words, she already knew what was on his mind and hers was now working overtime to come up with a new plan.

After all, Plan A – get the stubborn jackasses to _talk_ to each other – hadn’t netted the results _anyone_ had wanted. Therefore, Plan B was obviously necessary. The trick was figuring out what to do.

“We could lock them in a closet?” Charlie suggested.

“No, no, no, how about, a masquerade?” Jo offered as she leaned back in Charlies arms. Ash snorted.

“No way, kemosabe, nobody does shit like that anymore.” Deans family and friends were hanging out at the Roadhouse to discuss the ‘plan’. Benny’s might be the new go to place, but the Roadhouse was still a bar, and also boasted a pool table, darts and even a couple of old arcades. Not to mention, it was owned by Ellen Harvelle, who might have gone all squinty eyed when she realized her own family were frequenting a new place. The others rushed to assure her that it was like comparing apples and oranges and they wouldn’t be giving up the Roadhouse for love or money. She grunted an acknowledgement and went back to wiping down the bar, giving in and eavesdropping on their plotting instead.

“Well, how about – “ Garth started to speak and everyone shot him down before he could finish.

“Nope, they’ll never agree to those stupid games.” Jo added, not even trying to gentle her words. It didn’t matter, nothing ever seemed to faze Garth.

“What stupid games?” Sam said as he plunked down in a seat, Eileen right beside him. He nodded at Ellen and she nodded back, already setting the couple up with their usual order.

“Oh, you know, high school games, like uh, truth or dare, spin the bottle, seven minutes in heaven or uh, what’s that other one?” Jo answered Sam.

“Never have I ever…I think?” Castiel tentatively added. Jo nodded.

“Yeah, that’s the one.”

“Why are we talking about high school games?” Sam inquired after a sip of his beer.

“Trying to figure out how to push your brother and that gorgeous cook together. Why are they such stubborn little shits?”

“JoAnna Beth!” Ellen called from behind the bar.

“What? It’s not like we’ve never heard worse in here!” Jo waved her hand around to indicate the entire bar and Ellen rolled her eyes at her daughter.

“That’s not the point. Anyway, why’s it so important you get Dean together with this guy?” Ellen dropped all pretense of ‘not listening’ and leaned across the bar.

“Because the UST - not to mention the emotional constipation that accompanies it - is just about smothering us to death.” Sam bemoaned.

“So what’s the hang-up? I’ve never known Dean to be shy.” Ellen quirked an eyebrow at the gang arranged before her.

“We wish we knew. That would make this a whole hell of a lot easier.” Sam was getting ready to start banging his head on a flat surface again when Eileen caught his arm and grabbed his attention. When Sam looked at her she smiled.

“Why don’t we just set them up?” She asked. Everyone stared at her. She stared back. Had she not articulated her question well enough for them to understand. She started to raise her hands in concern, to sign what she’d said, but Sam covered them and held them in his own.

“We can’t set them up, that’s part of the problem. If we could just…get them to go out on a date, I’m sure it would all fall into place but…the two of them seem to shy away before anything of the like could be suggested.” Sam explained carefully. Had he really not told her all this yet?

“Oh, well, I wasn’t suggesting that we suggest, or even ask, either of them. We just do it.” All of them were staring at her now and she fidgeted a little uncomfortably. She glanced away from them back to Sam.

“Okay, but I still don’t get _how_?” he asked, the puzzlement on his face clear as day, even if she couldn’t hear it in his voice.

“Well, I was talking to Andrea earlier today, and she was telling me about a family event that Benny was dreading going to.  Seems they’ve been on his case to ‘find someone’ and settle down. Andrea was thinking, we could set them up by getting Dean to pretend to be Benny’s boyfriend for the event, get the family off his back. I’m sure if they spent more than five minutes at a time in each other’s company, things would have to come to a head somehow.”

The others nodded slowly at her words, looking around at each other thoughtfully. It was Ellen who spoke up first. “You think Dean’d go for it?”

“Hell, he would. Boy likes helpin’ people.” The gruff voice from the other end of the bar startled them all into turning and staring at Bobby Singer, Dean and Sam’s surrogate dad. “Worth a shot, then maybe you kids could come in here talkin’ ‘bout somethin’ other than yer love lives…”

Plan B was decided upon and all that was left was putting into motion. Couldn’t be too hard, could it?

* * *

 “What’s that now, cher?” Benny paused, uncertain as he stared at his ex wife again.

“I said that Sorento came by the other day, asking about you.”

“Well, why didn’t the old man talk to me himself?” Benny’s tone was disgruntled.

“Seems to think you’ve been avoiding him. Have you?” She countered, knowing full well what the answer would be. He was. Benny turned away from her and got back to work. They were closing up for the night and if he didn’t want to be stuck here till 6am, he needed to get back to work. She took his avoidance for what it was and simply continued talking. “He was talking about setting you up with one of his business partners."

Andrea smirked as she watched Benny shudder. Okay, so Sorento hadn’t actually said that. He had been hands off after the last time he’d tried to set up his son with that guy Desmond. It hadn’t gone well, to say the least. But Benny didn’t need to know that. If she could get him scared enough, he would definitely grasp at any solution she gave him. And between her and Eileen, they’d definitely come up with one.

She listened to him mutter to himself as she slid up next to him and helped him with the cleaning. “You know,” she paused dramatically to snap her fingers, as if the thought had just occurred to her, “If you maybe showed up at the family Christmas party this year with a date, he probably would stop trying to fix you up with other people, I mean, if it bothers you that much.”

“Darlin’, y’know I don’t get out much these days. An’ who would you suggest I ask to pretend to be mah boyfriend?”

“I’ve actually got some ideas. Why don’t you just leave it to me?” He eyed her suspiciously and she gave him the most innocent look she could muster. It must have worked because he shrugged and nodded.

“Fine. But whoever you find better not be as creepy as that Desmond was, or I’m bailin’ before we even get to any party.”

“What, you don’t think after fifteen years of marriage, I don’t know a thing or two about what you like? Give me some credit, Benny. Trust me, I’ve got your back.” She pretended to be affronted and he relented, the two of them getting back to cleaning up after a long night, more than ready to close up shop and head back to their respective places. For Benny, that would be the apartment upstairs, so at least he didn’t have to go far.

She held in her smirk and tried not to crow. She couldn’t wait to send Eileen a message. In fact – she glanced at her watch, then around at the kitchen. Everything was just about done, she could leave now without a guilty conscience. With a farewell to her ex husband, she made her way outside and to her car, pulling out her phone.

 

_::Well, I held up my side. He’ll never know what hit him.::_

_::Neither will Dean::_ Andrea finally allowed the smirk to come out and play, now that Benny could no longer bear witness to it, and sent back another text message in response to Eileen’s.

_::You’re up late. Or early. Didn’t expect such a fast response.::_

_::You try dealing with a sick moose all night and see how well you sleep.::_ Andrea frowned at the text message. What moose? A knock on her window broke her out of her singled minded focus on her phone and she glanced up, startled into dropping it, to find Benny frowning at her in concern. She breathed out a sigh of relief and rolled down the window.

“I’m fine, Benny, was just checkin’ my messages. I’m leaving now, I promise.”

“Nothin’ bad, now, is there Cher?”

“Of course not. I’d tell you if there was.” He nodded and let her go. She retrieved her phone, started the car and drove away feeling all sorts of smug, the odd comment about a moose long forgotten. She was too excited by the plan.

 

* * *

 

Sam blew his nose and then descended into a cough. His brother was by his side in an instant. Eileen and Dean had traded places early in the morning so she could finally get some rest, Dean instantly in the kitchen to make his mother’s patented tomato rice soup for his sick brother. He slid the steaming hot bowl in front of Sam and sat down beside him.

“You gonna be okay there, Sammy?”

“You and Eileen don’t have to baby me, man.”

“We’re not babying you!” Dean protested a little guiltily. Sam would have smirked if he’d had the energy, but right now he didn’t. The funny part was, this played perfectly into Eileen’s plan. It was almost like God had planned it like that. “Besides, is it a crime to help out your family?”

“Of course not Dean, I just…” Sam devolved into another round of hacking coughs and Dean pushed the bowl closer to him, slipping the spoon off the table and into the bowl. Sam glared. Dean stared back, unmoving. Sam made a big deal of sighing and grumbling before he reached for the spoon and slowly started eating the soup, blowing on each mouthful as he pondered how to say what he wanted to say and hoping his fever wasn’t affecting his judgement, or his words. “Look, man, you really wanna help me out?”

Dean nodded enthusiastically. “Of course I do. What’s up? What do you need?” He leaned forward and Sams’ weak but thankful smile.

“You got any plans for tonight? I had some, helping out a friend with a family issue, actually, but there’s no way I can help out in this state.”

“Nah, nothing important. What do you need? Who’s the friend?” Dean felt a little trepidation about blindly agreeing to whatever Sam needed – some of his friends were weird, and a lot of the shit he liked to do, Dean found completely boring – but his little brother was sick, and Winchesters didn’t bail on obligations. Besides, as Bobby had noted to the Roadhouse just a day or two before – unbeknownst to Dean of course – Dean just liked _helping_ people.

“Okay so, yeah, my friend’s family has been bugging him to find a boyfriend and settle down. They’ve even gone so far to set him up on a few dates but it’s never gone well. Apparently, the last guy was a real winner and he’s desperate to avoid his family’s help again. So we thought that maybe if he showed up to his family’s Christmas party with a date of his own, they’d let him off the hook for a while.”

Dean’s eyes narrowed at Sam’s words. He noticed that Sam hadn’t mentioned a name, but couldn’t figure out if it was deliberate or not. Sam might just be delirious because he was sick. And anyway, Dean could kind of sympathize with the guy, whoever he was, as he has had to deal with such well-meaning family members and friends himself.

“What’s Eileen think of this?” Dean noted disapprovingly. She was practically his sister in law already and he didn’t want Sam to mess up a good thing.

“Actually, it was her idea. It’s not like I’d actually be his boyfriend or anything. It’s just pretend. How hard can it be for a night? If I can help out a friend, I don’t see why I shouldn’t. Only I can’t.” Sam paused, letting the spoon drop into the bowl with a small splash, his hand trembling with the effort to hold it up, his stomach getting full. “You can do it, can’t you?”

Dean groaned as Sam pulled the puppy dog eyes TM on him and knew he was a goner. Only Sam had ever perfected that look against Dean, though their friend Castiel was a close second sometimes. “Fine, man, I’ll do it. Just tell me when and where.”

“Thanks Dean, it means a lot, to me _and_ my friend.”

“Yeah, but you still haven’t told me who it was.”

“I didn’t?” Sam feigned ignorance. At least he could get _something_ good out of being sick. “It’s that cook, Benny, down at at Benny’s.” Dean jolted and looked at his brother in surprise.

“Benny? I…I uh, I thought he was taken? I mean, him and the waitress there, that uh, dark haired one um, Andrea? They always seemed a little…chummy, if you um, know what I mean?”

Sam blinked at Dean’s disjointed sentence, picking it apart and finally piecing it together in his sick haze. He blinked again. Dean had thought - ? Well no wonder he’d been a stubborn ass…that was one thing you could say about Dean Winchester. He might have played the field when he was younger, and he was certainly equal opportunity and all that, but he never went after somebody who was in a relationship.

That certainly cleared up a lot of things. And made this a hell of a lot easier to boot. Sam felt his confidence in the plan increase almost a hundred fold. Not completely of course, because he still had no idea what was holding Benny back, but now that Dean knew Benny was a free agent, he’d be free to turn on the charm.

“Oh no,” Sam hastened to speak after realizing he’d gotten lost in his own thoughts. “No, I mean, they _were_ married I guess? Years ago? Even have a daughter together I think? But they’ve been divorced for a while. They opened the place together and it was an amicable divorce.  I guess it was Andrea who helped Benny figure out he was way more into men than women.”

“He is?” Dean’s voice _might_ have been a little hopeful and Sam restrained an urge to roll his eyes. It’d probably have just made him dizzy to do in his state anyway.

“Well, duh, man. I said he needed a boyfriend for this shindig, didn’t I?” Sam pushed his hand forward to grasp the soon again as Dean digested everything he’d learned in the last five minutes. Inwardly, Sam smirked. Dean was all reeled in. Hook, line and sinker.

Bingo.

* * *

Benny waited anxiously just inside the door of his restaurant. It felt weird not to be in the kitchen while it was open, but he wasn’t the only cook at Benny’s, and Andrea swore she had everything under control as she shoved him out with a last glimpse between the saloon style doors at his replacement, that guy Magnus he’d hired as his second a few months back. Weird name, but good at his job.

He looked out the front window. Andrea still hadn’t told him who his date was, just that he’d be arriving in a vintage muscle car. “I think he said it was a Chevy Impala, 1960 – something or other. Honestly, I wasn’t paying much attention. I’m not much into cars.”

He’d shaken his head at her in amusement, but it did nothing to stop the anxious pit in his stomach. He still wasn’t sure about this. Was it really better to try and get his father off his back with a pretend relationship? Surely the old man would see right through it? Through him? This could be a horrible evening. He sighed inaudibly and scrubbed a hand over his close-cropped beard. Think positive. He could always hit it off with his blind date. Then maybe he could get his father to stop trying to help _and_ he could finally get over Dean.

He knew the man didn’t do it on purpose – how could know, after all, that Benny had any kind of feelings for him? – but every time he came in for lunch or a special occasion, with that tall man of his (Sam, his brain supplied helpfully. He told his brain to shut up) it felt like they were taunting Benny with something just out of his reach. The man was gorgeous and everything he learned about him just…ugh, why did he have to be taken? Just his luck.

So his hopes for this evening was mostly to not crash and burn, but to also try and put everything behind him. Put Dean behind him. Wait, don’t think about that. Shit. The rumble of a vehicle made its way into the lot and he returned his attention out the window. Most cars these days were pretty damn quiet, which actually made him feel a little uneasy. Which meant this wasn’t a modern car, and he already knew he was looking for something not quite so modern.

He peered out against the darkening sky to see if he could recognize the Impala (he might have googled the make and model to see what it would look like. It had been a beautiful car…) and sure enough, there it was coming to a stop right outside the doors, idling with a loud purr.

With a sigh, Benny pushed open the doors and stepped outside. He hesitated before walking towards the vehicle, and nearly stumbled to a halt when the driver’s side open and Dean stepped out of the car, turned around and leaned across the roof with a grin. His mouth gaped.

What the hell was Dean doing here? Had he gotten the wrong car? He swept another look up and down the black muscle car before falling back on Dean again. Benny cleared his throat.  “Heya, Dean. That’s a mighty fine car ya got. It’s an Impala right?”

“You betcha – 1967, Chevy Impala. She’s a beaut right? Dad gave her to me when I turned 18. I keep my Baby purring like a kitten.” Benny watched Dean practically caress the car before beaming proudly at Benny. “’Sides, I couldn’t possibly come riding to your rescue on anything less than a mighty steed.” Dean winked at him and Benny almost felt his heart stop at the action _and_ the words.

“You sayin’ yer my knight in shining armor, brotha?” Benny had to get a hold of himself. Dean was just helping him out. Dean already _had_ a boyfriend. Benny needed to find a way to distance himself from the man across the car.

“Well, between you and me, the armor’s all on the car, but if the shoe fits…” He trailed off with a grin. “Why don’t you get in and you tell me where I’m going and what to expect?”

Benny nodded and reached for the door, sliding onto the leather seats with a contented sigh. He looked around at the pristine interior, so clean and well maintained. Well, of course, Dean _owned_ his own garage. Benny would expect nothing less of the man, especially with a car that obviously meant so much to him. He could certainly relate. Benny poured his own heart and soul into his restaurant.

They spent the ride to his fathers with Benny explaining what he and Dean would likely be walking into, often side tracking to this, that and the other thing. Benny had never spent quite so long in Dean’s presence before, always with pressing kitchen duties to attend to, and he found it so god damn easy to talk to the man. They could bond over the car, over food and, apparently, music. Dean had kept it low, but it was an appreciative Benny who felt soothed by the familiar classic rock tunes. It wasn’t the normal fare he played in his restaurant – didn’t exactly fit the theme after all – but he loved it, a fact that had both obviously surprised _and_ pleased Dean.

Which pleased Benny in turn before the conversation turned sour at the cruel, cruel reminder Dean negligently tossed out that this was not a _real_ date after all. “Yeah, Sammy’s always making fun of me for my music. It’s nice to have someone to talk to who can appreciate it for once. Hey, if nothing else, tonight has already been awesome. So don’t you worry, your dad? Won’t suspect a thing.”

Dean flashed him another grin before returning his attention back to the road. Benny felt like someone had upended a bucket of ice cold water over him and he went quiet. Dean let it go, seeming to think Benny was just enjoying the music and content to simply enjoy it with the other man.

If the car ride had started off easy and ended up a little strained, it served to show how the rest of the night was likely to go. They arrived at his father’s manor and Dean whistled his surprise but kept any remarks about it to himself, seeming to sense the nervousness Benny was feeling, even if he interpreted the reason for it wrong. Introductions ran smoothly, and as Dean had predicted, his family didn’t suspect a thing.

The party was small, smaller even then Benny had expected. His parents were there, of course, being the hosts, but his brothers had arrived with their families and Dean, he noted, had been surprised when Andrea finally arrived with a teenager in tow. Other than that, and themselves, that was it. No friends of the family. No work buddies. Benny had a sinking feeling it had been arranged this way so they could avail themselves of his ‘boyfriend’ and sound him out.

It would be a short while before dinner, and at one point Benny and Dean found themselves talking with Andrea and their daughter Elizabeth, who was quickly just as smitten with Dean as her father was. Just went to show, nobody was immune to the man’s charm. As Dean and Elizabeth talked, Andrea was quick to reassure him that Magnus had been doing fine, as had the other servers, when she’d left the restaurant.

“You worried about the place, man?” Dean asked Benny, handing him a glass like a thoughtful boyfriend would.

“A little bit, maybe.” Benny shrugged. Dean just laughed.

“Yeah, man, I get it. I feel like that any time I have to leave the shop for any reason. Don’t feel right. I mean, we’re our own bosses, right? We should be allowed to leave any time we wanted, but then ya feel guilty, am I right? Or that the folks you hired, who you know do their jobs perfectly fine – won’t be able to manage without you.”

“Yes, that’s it exactly.” Benny stared at him as Dean nodded sagely before giggling a little. The man quickly cut off the giggling with a more manly snort, but couldn’t help the odd chuckle or two that continued to escape.

Dinner was called soon and Dean was subjected to many more dishes that he was unfamiliar with but dug in with gusto anyway. Mouth full, he stared up at Benny’s amused eyes, and then looked around at the mixture of shocked and disgusted eyes from the rest of the family at the table. Benny admired Dean’s willingness to try ‘just about anything’ when it came to food (except that leafy shit. Cause what the fuck, I keep telling my brother I’m not a fuckin’ rabbit! Benny wondered when he’d meet this brother of his.) as Dean swallowed hastily and spoke up, “What? This is real good stuff!”

“Guess you’re dating the right man then, if you’re a fan of food in general and cuisine such as this.” Benny’s father spoke out in soft, deceptive tones.

“Well, yeah, I mean, Benny’s an awesome cook. How do ya think I met him? My brother convinced me to check his place out and we been going back for lunch every day since. Never regretted it. Helps that Benny here is just all sorts of awesome even outside the kitchen.” Dean beamed. Benny had to grip his fork tight as Dean’s words washed over him.

The only person Dean came in with, every day without fail, was that tall guy, Sam. But then that meant…could that really mean that…Benny’s breath stuttered as he blindly reached for his drink, taking a big gulp, Dean completely unaware of the bomb he’d dropped that had nearly stopped Benny’s heart – again.

Dean didn’t have a boyfriend. Sam was his brother. A literal, honest to god, blood brother. Fuck, Benny had been so fucking dumb. Why hadn’t he ever just _asked_? He tried to think through all their interactions. There was never anything Dean or Sam had said that would have led Benny to believe they were dating. And yet he had assumed just that.

So now, Dean’s willingness to help Benny out took on a new meaning, new possibilities. To be sure, he still could just be doing this as a favor. Dean might not even swing his way at all, but the biggest hurdle of them all had just been cleared. He had to believe this was a sign, and Dean didn’t seem they type to be offended if he learned Benny was into him, even if it turned out that he wasn’t in return.

So, what could it hurt to give it a shot? He just had to find the perfect moment.

 

* * *

 

Benny had been acting kind of strange all night, Dean thought. Running hot, then cold, he couldn’t figure the man out. He’d been wary, hesitant when it turned out Dean was the one that had shown up. But then he had seemed to warm up to him, only to shut down again just before they’d arrived.

Dean would have chalked that up to good old fashioned nervousness, except for what had happened at dinner. And he _still_ wasn’t sure what that had been. Things had seemed to be going well. Dean would have thought it odd to be meeting Benny’s ex – knowing now that they _were_ exes – followed by his kid, whom Dean had never met before. But that had gone well. Benny had been practically on top of him, never leaving his side for a moment, kept staring at him – and those were all good signs. But then he’d clam up, or verbally distance himself from Dean and it left him confused.

What the hell was going on?

And then dinner. He was pretty sure Benny’s family didn’t approve of him, for whatever reason. But something had shifted at dinner. Benny stood closer, stared longer with those almost sad looking baby blues, his grin was bigger and his laugh heartier. He didn’t seem like he was trying to distance himself any longer, but Dean couldn’t figure out what had changed.

Then again, should he be arguing it? This was what he wanted, right? A chance with Benny, an actual, _real_ chance to see if they could be something together. He’d almost resolved to make a move when Andrea came by passing out drinks and he realized that that must have been the change. Benny had had more than a couple drinks over the course of the night. Dean had been pacing himself because he was driving, but Benny had been nervous as hell. Dean couldn’t blame the man for fortifying himself with a few drinks.

This new, relaxed Benny might have nothing to do with Dean and everything to do with the alcohol. Which would make tonight the worst time ever to make a move. Fuck, he was never going to win, was he?

Eventually, it got late enough that people started departing and Benny looked over at Dean almost desperately. The ‘okay, we’ve done our part, now let’s get the hell out of dodge before I implode’ inherent in his look. Dean nodded and stood up, Benny standing along with him. Still playing the part of an attentive boyfriend – easy since he really did like Benny – his hand slid down to grab Benny’s thick fingers as Benny spoke.

“Looks like it’s time for us to get goin’. It was a wonderful meal and a wonderful time as always.”

“Of course, Benny. Why don’t you and your boyfriend come over again sometime soon. Don’t be strangers, now.” Sorento, the man Benny had introduced as his father, answered back. It sounded insincere and Dean suddenly couldn’t wait to get out of there.

“Um, so uh, were can we find our coats?” Dean and Benny beat a hasty retreat, only breathing easier once they sat inside the Impala. With a breathless laugh, Dean turned her on, both men relaxing at the soothing roar. Benny snickered and Dean looked at him.

“What is it?”

“My old man was watchin’ us from the door. I think he’s about to have a stroke over this car.”

“He got something against the classics?” Dean grumbled as he pulled away.

“Nah, I don’t think he gave you the credit you deserved, cher.” Dean felt his heart skip a beat at being called cher by Benny. He had quickly learned it was the burly mans’ term of endearment for those he cared about. He had a few, but cher seemed to be reserved for the inner circle. Did that mean…?

They chatted quietly off and on for the drive back to Benny’s. The lights were off since it was late enough for the place to be closed and the staff all gone home. Dean pulled in front of the doors again and Benny shook his head. “Drive ‘round back, cher. My apartment has a separate entrance.” Dean nodded and swung around, pulling to another stop. He didn’t look like he was going to turn off the car so Benny leaned over and did it for him.

Dean looked up at him in surprise. “Uh, Benny?”

“Look, cher, if I’m wrong, you just tell me right now, y’hear? But I been thinkin’ ‘bout this all night.” Benny snorted, “Longer even, I just didn’t realize you were available, if y’know what I mean.”

“I, uh…what?” Dean mentally cursed himself. _Smooth, Winchester, real smooth._ Did Benny mean what he thought he meant? But what was that about being available? He was so confused right now.

“I would like to kiss ya, Dean, now that I know Sam’s yer brother and not yer lover. If ye’d be interested, that is.” Benny leaned a little closer, but was careful not to crowd Dean, in case he was reading the man wrong.

Dean’s eyes widened and he spluttered. “You thought…me and Sam?” His voice squeaked indignantly at the thought. “Holy fuck…” Dean started laughing, tears started rolling out of his eyes. He tried to talk around the laughter, but it was difficult. “Fuck, Benny, so much wasted time. Y’know I thought you and Andrea were a thing? I mean, I guess you were, once upon a time, but I mean, _y’know_ , I thought you still were…I only found out this morning I was wrong. And this whole time, you’ve been thinking…me and _Sam?”_

Dean wasn’t sure how he got that out coherently with his hoots of laughter. He dropped his head onto the steering wheel as he wheezed and tried to get himself back under control. Cause fuck, Benny had asked to kiss him, and there was no way he was missing out on that.

He finally looked up to see a bemused Benny staring at him. There was a mixture of anticipation and dread on his face.  Dean sobered up instantly, realizing his reaction hadn’t done much to reassure the other man that his attentions were even wanted. He leaned forward, reaching a hand out to touch Benny’s face, rub his fingers down the glorious facial fuzz and watched the man’s lips part in surprise and hope, his tongue dipping out to lick at his lips. Dean was mesmerized by the motion but he needed to speak first, not allow himself to get lost in Benny as he had longed to do for so long.

“Look, Benny, I’d love to kiss ya, man, but I gotta know something first. How drunk are you? ‘Cause I ain’t kissing you if you’re drunk. I just…I need to know, okay?”

“I been drinking, Dean, sure, but I ain’t that drunk, I promise ya. And cher, alls I’m askin’ for tonight is a kiss. If yer interested.”

“Oh, trust me, I’m interested…” They held each other’s gazes for a long moment that clicked over to a few long moments before one of them – or maybe both of them – finally leaned forward and their lips met.

They kissed for a good long while as the car settled and cooled around them. Chaste, barely there kisses, intermixed with deeper, wetter ones. Eyes closing, groans and contented hums and the occasional wet sound filling the Impala’s interior before they finally broke away from each other.

“It’s getting kinda cold, guess I should let you get inside.” Dean noted reluctantly.

“Yeah, guess so.” Benny was just as reluctant to leave. He looked down to where their hands and fingers were intertwined and then back up. “So…we uh, we gonna start somethin’ cher?”

“I’d really like that.” Dean answered hopefully. “Take you out on a real date, man…”

Benny huffed out a laugh. “Yeah, meetin’ the family’s not the best first date, is it?”

“Well, I dunno, seems fair. You already met most of mine…”

Benny looked back up at Dean. “I just still can’t believe Sam was yer brother the whole time. Y’know the amount of pining I been doin’ every time ye came in?”

“Probably about the same as me. And the teasing I’ve endured…god, Sam’s gonna get it.” Dean groaned good-naturedly.

“Nah, don’t blame Sam. It’s thanks to him that we even met, after all.”

“Yeah, I suppose I can cut the kid some slack. This time.” Dean muttered before diving in for one last kiss.

Benny walked back to his apartment on cloud nine, laughing when he realized that Andrea had put mistletoe in the entryway, just in case. He turned to wave at Dean before the man drove away.

Turned out, they never needed it.

**Author's Note:**

> I'm afraid there's not much 'real' mention of christmas, but it was intended to be a christmas party that they went to, i did mention it was december and there was an arrangement for mistletoe - it just never got used.
> 
> hope it still counts?


End file.
